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W-Shaped π-Extended Double Undecabenzo[7]helicene.

Org Lett

September 2024

College of Chemistry, Beijing Normal University 19 Xinjiekouwai Street, Haidian District, Beijing 100875, People's Republic of China.

A chiral W-shaped fully π-extended double [7]helicene () has been synthesized and fully characterized. It displays fluorescence emission (λ = 636 nm) with a quantum yield (Φ) of 0.10.

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Aggregation-induced emission from optically active X-shaped molecules based on planar chiral [2.2]paracyclophane.

Sci Rep

December 2023

Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University, 1 Gakuen Uegahara, Sanda, Hyogo, 669-1330, Japan.

An optically active π-stacked molecule was synthesized incorporating planar chiral [2.2]paracyclophane and o-carborane units to impart circularly polarized luminescence and aggregation-induced emission properties to the molecule. The molecule exhibited a strong emission from the aggregated state in a mixed solvent system (HO/THF) and the solid state in the PMMA matrix.

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A series of π-extended salophen-type Schiff-base zinc(ii) complexes, , zinc-salophen complexes (ZSC), were investigated toward potential applications for dye-sensitized solar cells. The ZSC dyes adopt linear-, X-, or π-shaped geometries either with the functionalization of 1 donor/1 acceptor or 2 donors/2 acceptors to achieve a push-pull type molecular structure. The frontier molecular orbitals, light-harvesting properties as well as charge transfer characters against regio-specific substitution of donor/acceptor groups were studied by using density functional theory (DFT) and time-dependent density functional theory (TDDFT).

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Redox-induced reversible [2 + 2] cycloaddition of an etheno-fused diporphyrin.

Chem Sci

February 2021

Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University Furo-cho, Chikusa-ku Nagoya 464-8603 Japan

3,5-Ethenoporphyrin is a π-extended porphyrin containing a fused ethene unit between the - and β-positions, exhibiting unique contribution of macrocyclic antiaromaticity. We have recently reported that its analogue, etheno-fused diporphyrin, underwent thermal [2 + 2] cycloaddition to furnish X-shaped cyclobutane-linked tetraporphyrins. Here we demonstrate that the cyclobutane-ring formation is dynamically redox-active.

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Conformationally rigid X-shaped PAHs are attracting interest due to their self-assembly into unique networks and as models to study through-space exciton and charge delocalization in one single molecule. We report here the synthesis of X-shaped PAHs by dimerization of diazaheptacene diimides. The diimide groups are employed to effectively direct the self-assembly into antiparallel dimer aggregates, which assist the compounds to undergo a regiocontrolled [4 + 4] dimerization, leading to an X-shaped conformation bearing electron-poor and -rich subunits.

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